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Biosynthetic enzymes of antifouling halogenated compounds

Research Project

Project/Area Number 24380112
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Fisheries chemistry
Research InstitutionHokkaido University

Principal Investigator

Okino Tatsufumi  北海道大学, 地球環境科学研究科(研究院), 准教授 (30280910)

Co-Investigator(Kenkyū-buntansha) MATSUDA Fuyuhiko  北海道大学, 大学院地球環境科学研究院, 教授 (10219446)
UMEZAWA Taiki  北海道大学, 大学院地球環境科学研究院, 准教授 (20503618)
Co-Investigator(Renkei-kenkyūsha) NOGATA Yasuyuki  電力中央研究所, 環境科学研究所, 主任研究員 (10371535)
WASHIO Kenji  北海道大学, 大学院地球環境科学研究院, 助教 (50241302)
Project Period (FY) 2012-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥17,940,000 (Direct Cost: ¥13,800,000、Indirect Cost: ¥4,140,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2013: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2012: ¥8,320,000 (Direct Cost: ¥6,400,000、Indirect Cost: ¥1,920,000)
Keywords生合成 / 付着阻害 / フジツボ / 紅藻 / ブロモアレン / キプリス / ブロモペルオキシダーゼ / テルペノイド / タテジマフジツボ / マギレソゾ / ハチジョウジマレン / Omaezallene / Laurencin / ハロゲン / 付着生物 / ローレンシン / ウラソゾ
Outline of Final Research Achievements

Vanadium dependent bromoperoxidase (VBPO) was cloned from the red alga Laurencia nipponica which produces a halogenated compound, laurencin. The enzyme catalyzed cyclization and bromination of a precursor of laurencin. Bromination activity of recombinant enzyme was investigated. A similar type of VBPO was cloned from L. okamurae which produces a halogenated sesquiterpenoid, laurinterol. The recombinant enzyme showed bromination activity. In addition, another type of VBPO was cloned from L. saitoi which produces a halogenated triterpenoid. Its properties were investigated by using its recombinant protein. The structure of bromoallene containing C15 compound, omaezallene was reported. Its totaly syntehsis was successfully achieved.

Report

(5 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (21 results)

All 2016 2015 2014 2013 2012 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (17 results) (of which Invited: 3 results)

  • [Journal Article] Omaezallene from red alga laurencia sp.: Structure elucidation, total synthesis, and antifouling activity2014

    • Author(s)
      Umezawa, T., Oguri, Y., Matsuura, H., Yamazaki, S., Suzuki, M., Yoshimura, E., Furuta, T., Nogata, Y., Serisawa, Y., Matsuyama-Seisawa, K., Abe, T., Matsuda, F., Suzuki, M., Okino, T.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 53 Issue: 15 Pages: 3909-3912

    • DOI

      10.1002/anie.201311175

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] cDNA Cloning and Characterization of Vanadium-Dependent 3 Bromoperoxidases from the Red Alga Laurencia nipponica2014

    • Author(s)
      Kaneko, K., Washio, K., Umezawa, T., Matsuda, F., Morikawa, M. and Okino, T.
    • Journal Title

      Bioscience, biotechnology, and biochemistry

      Volume: 印刷中

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thrombin inhibitors from the freshwater cyanobacterium Anabaena compacta2012

    • Author(s)
      Anas, A. R., Okino, T., et al
    • Journal Title

      Journal of Natural Products

      Volume: 75 Issue: 9 Pages: 1546-1552

    • DOI

      10.1021/np300282a

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Confirmation of the Configuration of 10-Isothiocyanato-4-cadinene Diastereomers2012

    • Author(s)
      Nishikawa, K. Umezawa, T., et al
    • Journal Title

      Journal of Natural Products

      Volume: 75 Issue: 12 Pages: 2232-2235

    • DOI

      10.1021/np300439e

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] 紅藻マギレソゾLaurencia saitoi由来ブロモペルオキシダーゼの臭素付加反応2016

    • Author(s)
      正木志良、金子賢介、小林大毅、石川高史、西川慶祐、森本善樹、鷲尾健司、森川正章、沖野龍文
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌コンベンションセンター(札幌市)
    • Year and Date
      2016-03-30
    • Related Report
      2015 Annual Research Report
  • [Presentation] 紅藻ミツデソゾ(Laurencia okamurae)由来ブロモペルオキシダーゼの性状解析2016

    • Author(s)
      石川高史・金子賢介・湯暁蓉・鷲尾健司・森川正章・沖野龍文
    • Organizer
      化学系学協会北海道支部2016年冬季研究発表会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2016-01-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] Natural products as antifouling strategy - the case of compounds from organisms of the Red Sea2015

    • Author(s)
      Petitbois, Julie; Abdel-Lateff, Ahmed; Alarif, Walied M.; Ayyad, Seif-Eldin N.; Al-Lihaibi, Sultan S.; Yoshimura, Erina; Nogata, Yasuyuki; Okino, Tatsufumi
    • Organizer
      第4回ワークショップ「船底塗料と海洋環境に関する最新の話題」
    • Place of Presentation
      函館市国際水産・海洋総合研究センター(北海道函館市)
    • Year and Date
      2015-09-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] 紅藻ソゾ属3種のブロモペルオキシダーゼの活性評価2015

    • Author(s)
      金子賢介、小林大毅、鷲尾健司、森川正章、沖野龍文
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋市(日大)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Laurnecia属紅藻のブロモペルオキシダーゼ2014

    • Author(s)
      金子賢介、鷲尾健司、小林大毅、湯暁蓉、梅澤大樹、松田冬彦、森川正章、沖野龍文
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知市(県民文化ホール)
    • Year and Date
      2014-10-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] 八丈島産ソゾ属海藻より得られたタテジマフジツボ幼生付着阻害物質hachijojimallene AおよびBの構造2014

    • Author(s)
      小栗祐子・松浦裕志・吉村えり奈・野方靖行・沖野龍文
    • Organizer
      日本化学会北海道支部2014年夏季研究発表会
    • Place of Presentation
      苫小牧市(苫小牧高専)
    • Year and Date
      2014-07-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] Hachijojimallene Aの合成研究2014

    • Author(s)
      増田大海、梅澤大樹、松田冬彦
    • Organizer
      日本化学会北海道支部2014年夏季研究発表会
    • Place of Presentation
      苫小牧市(苫小牧高専)
    • Year and Date
      2014-07-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 藻類のつくる生物活性物質の構造多様性2014

    • Author(s)
      沖野龍文
    • Organizer
      生合成マシナリー特別シンポジウム第10回生合成マシナリー札幌セミナー
    • Place of Presentation
      札幌市(北大)
    • Year and Date
      2014-06-18
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 紅藻ウラソゾ Laurencia nipponica 由来バナジウム依存型ブロモペルオキシダーゼの性状解析2014

    • Author(s)
      金子賢介・鷲尾健司・梅澤大樹・松田冬彦・森川正章・沖野龍文
    • Organizer
      日本水産学会春季大会
    • Place of Presentation
      函館市 (北海道大学)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 紅藻ウラソゾと軟体動物クロヘリアメフラシから得られた付着阻害物質laurencin2013

    • Author(s)
      沖野龍文
    • Organizer
      日本水産学会
    • Place of Presentation
      東京海洋大学(東京都)
    • Year and Date
      2013-03-29
    • Related Report
      2012 Annual Research Report
  • [Presentation] オマエザレンの全合成と絶対立体化学の決定2013

    • Author(s)
      梅澤大樹、山崎翔平、小栗祐子、松浦裕志、鈴木将洋、沖野龍文、松田冬彦
    • Organizer
      第55回天然有機化合物討論会
    • Place of Presentation
      京都市 (同志社大学)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Vanadium dependent bromoperoxidase from the red alga Laurencia nipponica2013

    • Author(s)
      Kaneko, K., Washio, K., Umezawa, T., Morikawa, M., Matsuda, F., and Okino, T.
    • Organizer
      14th International Symposium on Marine Natural Products
    • Place of Presentation
      スペイン (La Toja Island)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 紅藻ウラソゾ Laurencia nipponica 由来バナジウム依存型ブロモペルオキシダーゼの性状解析2013

    • Author(s)
      沖野龍文・鷲尾健司・森川正章、松田冬彦、梅澤大樹
    • Organizer
      第 15 回マリンバイオテクノロジー学会大会
    • Place of Presentation
      沖縄県(市町村自治会館)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Antifouling activity and biosynthesis of brominated compounds from the red algae Laurencia spp2013

    • Author(s)
      Okino, T.
    • Organizer
      RACI NSW Natural Products Goup Annual One-Day Symposium
    • Place of Presentation
      オーストラリア (The University of New South Wales)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Chemistry and biology of brominated compounds from marine algae Laurencia spp.2013

    • Author(s)
      Okino, T.
    • Organizer
      The 2nd International Conference of the Indonesian Chemical Society
    • Place of Presentation
      インドネシア (イスラムインドネシア大学)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 紅藻ミツデソゾLaurencia okamurae のバナジウム依存型ブロモペルオキシダーゼの性質

    • Author(s)
      湯暁蓉・金子賢介・鷲尾健司・森川正章・沖野龍文
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見市(北見工大)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Omaezallene の全合成

    • Author(s)
      山﨑翔平・梅澤大樹・松田冬彦
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見市(北見工大)
    • Related Report
      2013 Annual Research Report

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Published: 2012-04-24   Modified: 2019-07-29  

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